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Diandra Chamberlain has worked in a variety of roles since 2014. Diandra began their career as a Student Caller at the UVM Foundation in 2014, then moved on to a Second Assistant Manager role at Yankee Candle in 2016. In 2017, they became a Travel Consultant at Liberty Travel, followed by a Business Development Manager role at Khitomer Solutions in 2019. In 2021, Diandra began working at Class Action Capital as a Business Development Associate and Contract Sales Specialist. Additionally, they are currently an Admissions Advisor at Thrive DX.

Diandra Chamberlain attended the University of Vermont from 2013 to 2017, earning a Bachelor of Arts in both International/Global Studies and Spanish Language and Literature. In 2016, they also studied at the Universidad de Sevilla.